Every year on Halloween, Toronto’s Gay Village transforms into a massive street party. Like an autumnal bonus Pride filled with booze and shivering twinks, Church Street shuts down to traffic and encourages thousands of queers to get “spoopy” with it. Visitors are emphatically encouraged to wear their most outlandish costumes and each business books the best drag they can afford months in advance. Queers of all ages endure various tortures (assorted Ontario public transit routes) to come party, people watch, and publicly projectile vomit in what is ostensibly the glory of nondenominational Gay Christmas. But where did all this start? Is this just a fruity version of a block party with a particularly PnP friendly BIA? Much like anything in queer history, the tradition of Halloween on Church can be traced back to a bunch of fierce drag queens who’d had enough.
The “Three Article Rule”
Quick! Are you wearing the right underwear to keep the cops off you?
By the 1950s, the so-called “three article rule” was a common phrase among queers in North America. The premise was simple; if a cop thought you were a man dressing a little too limp-wristed or a butchy boi with only metaphorical balls, he’d cuff you right then and there unless you could prove you were wearing at least three articles of clothing belonging to whatever sex he thought you should be. Invariably, this proof always involved the all-important underwear check. However, the term “three article rule” doesn’t actually appear in any legal document or handbook of protocols for how these gendered clothing checks are supposed to go down. And while explicit anti-crossdressing laws have existed in various American cities since 1848, there is no direct equivalent in Canadian law. Of course, this didn’t stop Toronto Police Services from cavorting around gay gathering grounds and stopping genderqueer people on the street to thin-blue-line their way to a humiliating parade of shorts and knickers.
Whether crossdressing was actually illegal or not, Toronto drag queens and genderqueers knew they’d be popped either way. The one exception was Halloween. On Halloween, costumes cross gender binaries, humans become monsters, and cops can’t be fucked to deal with any of it. It was the one night of the year you could put on that little strapless number with the matching lacy underthings with plausible deniability. Afterall, if the straights are going to treat gay gender expression as a horror, you might as well lean into it. Gay bars held best costume contests and drag balls for queens to compete for cash prizes and at least a year’s worth of bragging rights.
Before Church and Wellesley was Church and Wellesley
Letros Tavern Vertical File, The ArQuives.
Photograph by Atticus Hawk.
In the 40s and 50s, the gay bars of Church Street were decades away. Opened in the late 1940s, Letros at 50 King Street East was the first exclusively gay and lesbian bar in Toronto. This local haunt held a Halloween Ball every year with some sources indicating the festivities were regular events as early as 1959. Located across from the mildly gay friendly back bar in the King Edward Hotel, Letros was a two-minute jaunt from Toronto’s first gay area. Tucked into Toronto’s First Chinatown, this area was a collection of bars at the intersection of Queen and Bay, known to locals as simply “The Corners.”
In the 1950s, the city expropriated buildings throughout Toronto’s First Chinatown to build what would soon become Nathan Phillips Square and New City Hall. As a result, The Corners fell. Wellesley Station opened as part of the original Yonge subway line in 1954 with the first modern apartment complexes in the city opening its doors just a few streets away in 1957. Affluent gay men flocked in droves to these swingin’ bachelor lifestyle apartments, and Toronto gay nightlife began populating the strip of Yonge Street from College to Bloor.
In 1965, the straight owners of Letros banned costumes of any kind from the bar due to the constant police presence. As a result, the drag community headed up to the Yonge Street strip and settled into the St. Charles Tavern at 484 Yonge Street and the Parkside Tavern nearby at 530. Built in the 1870s as part of Toronto Fire Hall No. 3, the St. Charles Tavern’s distinct clock tower made it an easy meeting place for the bar’s regulars and new visitors alike.
City of Toronto Archives.
Photograph by Atticus Hawk.
The St. Charles hosted regular drag shows and soon became the iconic place for Halloween Drag Balls and contests. While the bar’s prominent clock tower and excellent proximity to transit options made it quite accessible to traveling queers, it also made it possible for homophobes to stop on by for a bit of Halloween bashing. By the mid 60s, crowds of aggressive onlookers would line up across the street to catch a glimpse of the decadent costumes and spit some hate at the queens. Popular radio DJs would rile up their listeners about the Halloween balls, and the media deemed the queens walking the block between venues, from the Parkside Tavern down to the St. Charles, “a parade.”
By the early 70s, these crowds were throwing eggs and beer bottles at the queens as the police set up metal barricades for “protection,” forcing St. Charles patrons up against the crowds if they wanted to get in. On Halloween 1976, four people were arrested, with police later finding several gasoline bombs behind the bar. In 1979, in direct response to the violence on Halloween and the lack of police intervention, the Toronto chapter of the Gay Alliance Toward Equity (GATE) formed operation “Jack O’Lantern.” Splitting into four teams of ten, each team included a lawyer and a trained first-aid person. These teams patrolled the area on Halloween night, escorting fellow queers to and from venues and pointing out obvious opportunities for intervention to cops who clearly needed a bit of direction.
Take Me to Church
While the St. Charles and other Yonge Street bars were a good place to party and cruise, the straight owners were often hostile to their gay patrons and regularly cooperated with police busts. After the 1977 push to “clean up” Yonge Street and the 1981 Bathhouse Raids that resulted, the Toronto queer community migrated one major intersection east to Church Street.
Bordered by the 519 Community Centre (opened in 1976) to the north, the predominantly gay apartment complexes to the west, and the popular cruising park of Allen Gardens to the south, gay-owned and operated businesses and bars began to flourish within the Church-Wellesley corridor.
Halloween on Church is a party. But it’s also a physical manifestation of drag queens who demanded their right to party just as much as anyone else. When you go out to gag on what’s being served and scream the night away to Britney, remember the people who fought for your right to do it. And don’t forget to eat a piece of fun-sized candy for every queen who ever looked like a goddamned star underneath that clock tower.
NOTES
“A Gay T.O. Rewind.” Alex Rowlson, 2005. Fab: Toronto’s Gay Scene/Lifestyle Magazine, no. 272.
“A look back at Toronto’s St Charles Tavern.” Xtra Magazine, YouTube, 2009. https://youtu.be/P0_OPFDqxUw
“Arresting Dress: Cross-Dressing, Law, and Fascination in Nineteenth-Century San Francisco.” Clare Sears, 2015. Duke University Press.
“Halloween Balls at The Letros and St. Charles Taverns.” The ArQuives: Canada’s LGBTQ2S+ Archives. https://digitalexhibitions.arquives.ca/exhibits/show/halloween-letros-stcharles
“Halloween in Toronto: Queen City of Canada.” 1964. Two Magazine, no. 4.
“Halloween on Yonge St. Poster.” GATE, 1979. Poster in CLGA archives (now The ArQuives: Canada’s LGBTQ2S+ Archives).
“How Dressing in Drag Was Labeled a Crime in the 20th Century.” Hugh Ryan, 2019. https://www.history.com/news/stonewall-riots-lgbtq-drag-three-article-rule
“The First Modern Apartment Complex in Toronto.” Chris Bateman, 2017. https://spacing.ca/toronto/2017/08/26/first-modern-apartment-complex-toronto/
“What a Drag.” Jeremy Parkes, 2000. Fab: Toronto’s Gay Scene/Lifestyle Magazine, no. 150.
Atticus Hawk (they/he) is a doctoral candidate in the Faculty of Information at the University of Toronto. His research looks at the role of Leatherdykes in the creation of medical knowledge and harm-reduction practices for fat, trans and disabled bodies in kink.